Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum

Masaki Kita, Masami Watanabe, Noboru Takada, Kiyotake Suenaga, Kaoru Yamada, Daisuke Uemura

研究成果: Article

8 引用 (Scopus)

抄録

Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. The stereostructure of hedathiosulfonic acid A was determined by the analysis of its degradation product, a cyclic β-hydroxysulfone. Hedathiosulfonic acids exhibited acute toxicity. We carried out various model reactions of the olefinic compounds with thiosulfonic acids and proved that, as is the case with natural products, synthesized thiosulfonic acid possessing a carbon-carbon double bond was converted into β-hydroxysulfone in the presence of oxygen.

元の言語English
ページ(範囲)6405-6412
ページ数8
ジャーナルTetrahedron
58
発行部数32
DOI
出版物ステータスPublished - 2002 8 5
外部発表Yes

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Thiosulfonic Acids
Sea Urchins
Acids
Carbon
Methylation
Biological Products
Toxicity
Nuclear magnetic resonance
Oxygen
Degradation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

これを引用

Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum. / Kita, Masaki; Watanabe, Masami; Takada, Noboru; Suenaga, Kiyotake; Yamada, Kaoru; Uemura, Daisuke.

:: Tetrahedron, 巻 58, 番号 32, 05.08.2002, p. 6405-6412.

研究成果: Article

Kita, Masaki ; Watanabe, Masami ; Takada, Noboru ; Suenaga, Kiyotake ; Yamada, Kaoru ; Uemura, Daisuke. / Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum. :: Tetrahedron. 2002 ; 巻 58, 番号 32. pp. 6405-6412.
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T1 - Hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum

AU - Kita, Masaki

AU - Watanabe, Masami

AU - Takada, Noboru

AU - Suenaga, Kiyotake

AU - Yamada, Kaoru

AU - Uemura, Daisuke

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N2 - Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. The stereostructure of hedathiosulfonic acid A was determined by the analysis of its degradation product, a cyclic β-hydroxysulfone. Hedathiosulfonic acids exhibited acute toxicity. We carried out various model reactions of the olefinic compounds with thiosulfonic acids and proved that, as is the case with natural products, synthesized thiosulfonic acid possessing a carbon-carbon double bond was converted into β-hydroxysulfone in the presence of oxygen.

AB - Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. The stereostructure of hedathiosulfonic acid A was determined by the analysis of its degradation product, a cyclic β-hydroxysulfone. Hedathiosulfonic acids exhibited acute toxicity. We carried out various model reactions of the olefinic compounds with thiosulfonic acids and proved that, as is the case with natural products, synthesized thiosulfonic acid possessing a carbon-carbon double bond was converted into β-hydroxysulfone in the presence of oxygen.

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KW - Natural thiosulfonic acid

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